Why We Keep Making Plans We Secretly Hope Get Cancelled

Dec 1, 2025

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Hannah Feminella

Let’s not pretend we haven’t all done it.

You make the plan. You confirm the time. You even pick the place. You enthusiastically text “Can’t wait!!!” with the correct number of exclamation points to signal the appropriate level of excitement. And then, like clockwork, 4:27 PM hits… and suddenly you’re praying for a cancellation. Not just hoping, fucking manifesting. You refresh the group chat like it owes you money. You read every “omw!” as a personal attack. You even consider faking a migraine, just to get out of something you agreed to two days ago. Why? What is this? When did showing up become the emotional equivalent of climbing Everest?

The truth is both embarrassing and universal: a lot of us don’t want to hang out…we just want to be invited.

We say yes because we meant it in the moment. Because the idea of the plan felt good. Romantic, even. But by the time the day rolls around? Real life sets in. Work drained you. Your social battery’s flickering. Your couch looks hot. And suddenly, that cute rooftop drink turns into a looming obligation that makes you want to fake your own death.

But here’s the thing we don’t talk about: we keep doing this. Over and over again. Making plans we low-key hope get cancelled. Then feeling guilty when they don’t. Then rescheduling. Then cancelling. Then repeating. It’s not just flaky—it’s a symptom of something deeper. We’re lonely. We’re tired. We’re overstimulated. And we’re terrible at saying, “I need connection, but I also need rest.” So instead, we schedule connection like productivity. We pencil it in. We commit to it in our calendars. We say yes on Monday and feel the dread by Thursday. And we wonder why our social lives feel more like a job than a joy.

Here’s what we need to start admitting: we don’t want more plans. We need better ones.

We want low-effort, high-reward hangs. We want the kind of connection that feels like exhaling, not performing. Just time. A drink. A place. Presence. That’s exactly why Joe and I built this new version of First Round’s On Me. So the endless “What time? Where? Who’s down? Ugh, never mind” spiral becomes four deliciously simple decisions: drink, time, place, and with who. That’s it

We wanted to give people plans that match capacity.  Plans that actually leave the group chat, and don’t leave you emotionally bankrupt. Then, we literally reward for showing up. Because the real solution isn’t cancelling more plans. It’s making plans that feel like a reward, not a burden, in the first place.

So the next time you're tempted to say “Yes!” out of obligation, pause. Ask yourself: Do I want to go? Or do I just want to be thought of? Needed? Included? That clarity changes everything. Because showing up shouldn’t feel like a performance. It should feel like a release. And the best plans? The ones you don’t secretly hope get cancelled? Those are the ones worth keeping. Until next time x

Social Club - The First Round's on Me Cafe

109 W 25th St New York, NY 10001 United States

Social Club - The First Round's on Me Cafe

109 W 25th St New York, NY 10001 United States

Social Club - The First Round's on Me Cafe

109 W 25th St New York, NY 10001 United States